Water-soluble surfactant compositions having improved taste

ABSTRACT

Treated surfactant composition containing a water-soluble surfactant and exhibiting improved taste, said composition comprising: a water-soluble surfactant selected from alkyl phosphate surfactants, alkyl phosphate ethoxylated surfactants, betaine surfactants, betaine ethoxylated surfactants, amine oxide surfactants, and mixtures thereof and water; wherein the composition further comprises: less than about 4%, by weight of the water-soluble surfactant, of total undesirable non-polar materials; less than about 2.5%, by weight of the water-soluble surfactant, of alcohols having a carbon chain length of greater than 4; less than about 1%, by weight of the water-soluble surfactant, of amine and amide materials; and less than about 1%, by weight of the water-soluble surfactant, undesirable non-polar materials selected from aldehydes, esters, ketones, and organic acids. Such compositions wherein the compositions have been subjected to liquid-liquid extraction processes.

CROSS REFERENCE TO RELATED APPLICATION

This reference claims priority to U.S. Provisional Application No.61/514,198, filed on Aug. 2, 2011, which is incorporated herein byreference.

FIELD OF THE INVENTION

The present invention relates to treated surfactant compositions havingimproved taste, such compositions containing water-soluble surfactant,reduced levels of undesirable non-polar materials, and water.

BACKGROUND OF THE INVENTION

Traditionally, much effort has been expended to improve the taste,color, odor or clarity of oral care compositions such as dentifrice(toothpaste), mouth rinse, and the like. Because of the nature of suchcompositions, the taste of a product may often be of more importance toconsumers than the actual or perceived efficacy. Since many efficaciousoral care components have undesirable taste, color, odor or clarity,efforts to improve these characteristics are common in the art. Fortaste, one way to remedy an undesirable product taste is to addadditional components, such as flavors, that will improve the overalltaste experience for the consumer. However, such remedies can beexpensive and it may be difficult to entirely mask an undesirable taste.Improvement of color or clarity through dyes or other additives hassimilar issues.

Water-soluble surfactants such as alkyl phosphate surfactants arecommercially available for use in a variety of consumer products,including oral care compositions. These anionic surface activeorganophosphate agents have a strong affinity for enamel surface andhave sufficient surface binding propensity to desorb pellicle proteinsand remain affixed to enamel surfaces. Such properties make thesematerials desirable for incorporation in oral care compositions such astoothpaste. However, these materials have not been widely commercializedin oral care compositions, despite their desirable properties. Onereason for this lack of commercialization may be the negative tasteand/or odor profile commonly associated with commercially availablealkyl phosphate materials. Although taste may not be a consideration inother consumer product industries, such as laundry, shampoo or personalcleansing, it is an important consideration in oral care. Similarly,while any undesirable odor associated with materials used in laundry,shampoo or personal cleansing products can typically be remedied by theaddition of perfume, perfume levels must be kept to a minimum in oralcare compositions for consumer acceptance and could produce furtherunpleasant tastes when utilized.

Purification of surfactant materials through steam-stripping,vacuum-stripping, and/or carbon filtration processes is also generallyknown to beneficially remove impurities to increase efficacy, minimizeundesirable side reactions, and the like. However, these purificationprocesses have been found to be insufficient to remedy the unpleasanttastes and/or odors associated with commercially available water-solublesurfactant materials.

Liquid/liquid extractions (LLE) are generally known in the art as usefulfor separating components of a mixture, wherein the constituents havediffering polarities which can be separated when mixed within twoimmiscible solvents that form a liquid bilayer after mixing. Forexample, LLEs are useful for purifying or cleaning samples which containimpurities of significantly differing polarity than the majority ordesirable component(s) of the sample. This can be achieved by mixing asample with a solvent that is immiscible with the primary liquid inwhich the sample is dissolved.

LLE has been utilized in chemical processing to reduce or eliminateundesirable by-products or contaminants. For instance, PCT PatentApplication WO 2008005550 to Hoke, et al (Procter & Gamble) discloses awater washing procedure to remove polar sulfur impurities frompeppermint oils to avoid malodor formation when formulated in dentifricecontaining stannous ions. In U.S. Pat. No. 4,352,829 to Noyes, et al(Procter & Gamble) an ethyl acetate extraction of caffeine from coffeewas shown to be an effective decaffeination process.

However, there is still an interest in finding ways to improve theoverall taste and/or odor of water-soluble surfactants such as thoseused in an oral care composition that are efficacious, cost-effective,and desirable to consumers.

SUMMARY OF THE INVENTION

It has now surprisingly been found that liquid-liquid extractionprocesses utilizing solvents such as ethyl acetate may be useful tosignificantly reduce the occurrence of non-polar materials found inwater-soluble surfactant raw materials and thereby improve thesurfactant's odor and/or taste profile.

Without being limited by theory, it is now believed that water-solublesurfactants previously generally thought to have bad taste and/or odorprofiles stemming from the pure material itself are in fact surprisinglyacceptable in terms of taste and odor. It has been surprisingly foundthat non-polar materials commonly present in commercially availablewater-soluble surfactant compositions such as residual alcohols, alcoholethoxylates, aldehydes, ethers, ketones, alkylamines, and esters, may belinked to the majority of the negative taste and odor profilespreviously associated with the surfactants themselves. Since some ofthese materials are often used in flavors and perfumes, it was furthersurprising that a new process for more efficiently extracting thesematerials from the underlying surfactant would produce such results. Forexample, dodecanol and dodecanal are commonly taught to be safe anduseful for inclusion in flavors and perfumes, yet it has beensurprisingly found that if included in water-soluble surfactantcompositions at significantly higher levels, these materials present anunpleasant taste such as bitter, soapy and the like.

Further without being limited by theory, liquid-liquid extraction usingthe appropriate solvent is more effective than previously knowntechniques to purify such surfactants, allowing for the incorporation ofsuch surfactants into oral care products with minimal negative tasteand/or odor attributes.

The present invention is therefore directed to treated surfactantcompositions containing a water-soluble surfactant and exhibitingimproved taste, said composition comprising: from about 10% to about94%, by weight of the composition, of a water-soluble surfactantselected from alkyl phosphate surfactants, alkyl phosphate ethoxylatedsurfactants, betaine surfactants, betaine ethoxylated surfactants, amineoxide surfactants, and mixtures thereof; and from about 3% to about 90%,by weight of the composition, of water; wherein the composition furthercomprises: less than about 4%, by weight of the water-solublesurfactant, of total undesirable non-polar materials; less than about2.5%, by weight of the water-soluble surfactant, of alcohols having acarbon chain length of greater than 4; less than about 1%, by weight ofthe water-soluble surfactant, of amine and amide materials; and lessthan about 1%, by weight of the water-soluble surfactant, undesirablenon-polar materials selected from aldehydes, esters, ketones, andorganic acids.

In one embodiment, the present invention relates to such compositionswherein the water-soluble surfactant is at least about 30% soluble inwater.

In one embodiment, the present invention relates to such compositionswherein the water-soluble surfactant is selected from cocoamidopropylbetaines, lauryl betaines, capryl/capramidobetaines, mono alkylphosphates, alkyl ethoxylated surfactants, amine oxides, and mixturesthereof.

In one embodiment, the present invention relates to such compositionswherein the water-soluble surfactant is selected from cocoamidopropylbetaines, mono alkyl phosphates, alkyl ethoxylated surfactants, andmixtures thereof.

In one embodiment, the present invention relates to such compositionswherein the water soluble surfactant is an ethoxylated mono alkylphosphate surfactant.

In one embodiment, the present invention relates to such compositionswherein the composition comprises from about 10% to about 50%, by weightof the composition, of water-soluble surfactant.

In one embodiment, the present invention relates to such compositionswherein the composition comprises less than about 2%, by weight of thewater-soluble surfactant, of undesirable non-polar materials.

In one embodiment, the present invention relates to such compositionswherein the composition comprises from about 3% to about 20%, by weightof the composition, of water.

In one embodiment, the present invention relates to such compositionswherein the composition comprises less than about 1%, by weight of thewater-soluble surfactant, of alcohols having a carbon chain length ofgreater than 4.

In one embodiment, the present invention relates to such compositionswherein the composition comprises from about 20% to about 30%, by weightof the composition, of the water-soluble surfactant; from about 60% toabout 90%, by weight of the composition, of water; and less than about2%, by weight of the water-soluble surfactant, of total alcohols havinga carbon chain length of greater than 4.

In one embodiment, the present invention relates to such compositionswherein the composition has been subjected to a liquid-liquid extractionprocess.

The present invention further relates to treated surfactant compositionscontaining a mono alkyl phosphate surfactant and having improved taste,said composition comprising: from about 10% to about 94%, by weight ofthe composition, of mono alkyl phosphate surfactant; from about 3% toabout 90%, by weight of the composition, of water; less than about 4%,by weight of the water-soluble surfactant, of undesirable non-polarmaterials; and less than about 2.5%, by weight of the water-solublesurfactant, of alcohols having a carbon chain length of greater than 4.

In one embodiment, the present invention relates to such compositionswherein the composition comprises less than about 0.5%, by weight of themono alkyl phosphate surfactant, of alcohols having a carbon chainlength of greater than 4.

In one embodiment, the present invention relates to such compositionswherein the surfactant is selected from cocoamidopropyl betaines andcomprises less than about 3%, by weight of the cocoamidopropyl betainesurfactant, of undesirable non-polar materials; and comprises less thanabout 1%, by weight of the cocoamidopropyl betaine surfactant, of amineand amide materials.

In one embodiment, the present invention relates to such compositionswherein the composition comprises less than about 0.25%, by weight ofthe cocoamidopropyl betaine surfactant, of amine and amide materials.

The present invention further relates to treated surfactant compositionscontaining a water-soluble surfactant and having improved taste, saidcomposition consisting essentially of: from about 10% to about 94%, byweight of the composition, of a water-soluble surfactant; from about 3%to about 90%, by weight of the composition, of water; and less thanabout 1%, by weight of the water-soluble surfactant, of undesirablenon-polar materials.

The present invention further relates to oral care compositionscomprising such surfactant compositions.

The present invention further relates to such oral care compositionsthat are in a form selected from toothpaste, dentifrice, tooth gel,subgingival gel, mouthrinse, mousse, foam, mouthspray, lozenge, chewabletablet, chewing gum or denture product.

The present invention further relates to such oral care compositionswherein the oral care composition is incorporated onto strips or filmsfor direct application or attachment to oral surfaces.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to treated water-soluble surfactantcompositions having improved taste. Such compositions contain from 10%to about 94%, by weight of the composition, of a water-solublesurfactant selected from alkyl phosphate surfactants, alkyl phosphateethoxylated surfactants, betaine surfactants, betaine ethoxylatedsurfactants, amine oxide surfactants, and mixtures thereof; and fromabout 3% to about 90%, by weight of the composition, of water; whereinthe composition further comprises: less than about 4%, by weight of thewater-soluble surfactant, of total undesirable non-polar materials; lessthan about 2.5%, by weight of the water-soluble surfactant, of alcoholshaving a carbon chain length of greater than 4; less than about 1%, byweight of the water-soluble surfactant, of amine and amide materials;and less than about 1%, by weight of the water-soluble surfactant,undesirable non-polar materials selected from aldehydes, esters,ketones, and organic acids.

In one embodiment, the treated water-soluble surfactant composition hasbeen previously subjected to a liquid-liquid extraction process.

These elements will be discussed in more detail below.

Water-Soluble Surfactant

The compositions of the present invention contain from about 10% toabout 94%, by weight of the composition of a water-soluble surfactant.In one embodiment, the compositions of the present invention containfrom about 10% to about 70%, 10% to about 50%, alternatively from about20% to about 30%, by weight of the composition, of a water-solublesurfactant.

As used herein “water-soluble surfactant” refers to those surfactantsthat are at least partially soluble in water, when measured at roomtemperature (25° C.). In one embodiment, the water-soluble surfactant isat least 10% soluble in water, alternatively is at least 20% soluble inwater, and still alternatively is at least 30% soluble in water,alternatively at least 40% soluble in water.

Examples of water-soluble surfactants useful herein includecocoamidopropyl betaines, lauryl betaines, capryl/capramidobetaines,mono alkyl phosphates, alkyl ethoxylated phosphates, amine oxides, andmixtures thereof.

Water-soluble surfactants useful herein may, in some embodiments beselected from anionic surfactants such as alkyl phosphates. Thesesurface active organophosphate agents have a strong affinity for enamelsurface and have sufficient surface binding propensity to desorbpellicle proteins and remain affixed to enamel surfaces. Suitableexamples of organophosphate compounds include mono-, di- or triestersrepresented by the general structure below wherein Z1, Z2, or Z3 may beidentical or different, at least one being an organic moiety, in oneembodiment selected from linear or branched, alkyl or alkenyl group offrom 1 to 22 carbon atoms, optionally substituted by one or morephosphate groups; alkoxylated alkyl or alkenyl, (poly)saccharide, polyolor polyether group.

Some other agents include alkyl or alkenyl phosphate esters representedby the following structure:

wherein R1 represents a linear or branched, alkyl or alkenyl group offrom 6 to 22 carbon atoms, optionally substituted by one or morephosphate groups; n and m, are individually and separately, 2 to 4, anda and b, individually and separately, are 0 to 20; Z2 and Z3 may beidentical or different, each represents hydrogen, alkali metal,ammonium, protonated alkyl amine or protonated functional alkyl aminesuch as an alkanolamine, or a R1-(OCnH2n)a(OCmH2m)b-group. Examples ofsuitable agents include alkyl and alkyl (poly)alkoxy phosphates such aslauryl phosphate; PPG5 ceteareth-10 phosphate; Laureth-1 phosphate;Laureth-3 phosphate; Laureth-9 phosphate; Trilaureth-4 phosphate; C12-18PEG 9 phosphate; Sodium dilaureth-10 phosphate. In one embodiment, thealkyl phosphate is polymeric. Examples of polymeric alkyl phosphatesinclude those containing repeating alkoxy groups as the polymericportion, in particular 3 or more ethoxy, propoxy isopropoxy or butoxygroups.

Zwitterionic or amphoteric surfactants useful in the present inventioninclude derivatives of aliphatic quaternary ammonium, phosphonium, andsulfonium compounds, in which the aliphatic radicals can be straightchain or branched, and wherein one of the aliphatic substituentscontains from about 8 to 18 carbon atoms and one contains an anionicwater-solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphateor phosphonate. Suitable amphoteric surfactants include betainesurfactants such as disclosed in U.S. Pat. No. 5,180,577 to Polefka etal. Typical alkyl dimethyl betaines include decyl betaine or2-(N-decyl-N,N-dimethylammonio) acetate, coco betaine or2-(N-coco-N,N-dimethyl ammonio) acetate, myristyl betaine, palmitylbetaine, lauryl betaine, cetyl betaine, stearyl betaine, etc. Theamidobetaines are exemplified by cocoamidoethyl betaine, cocamidopropylbetaine (CAPB), and lauramidopropyl betaine. The unwanted tastes oftenassociated with these surfactants are soapy, bitter, chemical, and/orartificial.

Additional suitable polymeric organophosphate agents include dextranphosphate, polyglucoside phosphate, alkyl polyglucoside phosphate,polyglyceryl phosphate, alkyl polyglyceryl phosphate, polyetherphosphates and alkoxylated polyol phosphates. Some specific examples arePEG phosphate, PPG phosphate, alkyl PPG phosphate, PEG/PPG phosphate,alkyl PEG/PPG phosphate, PEG/PPG/PEG phosphate, dipropylene glycolphosphate, PEG glyceryl phosphate, PBG (polybutylene glycol) phosphate,PEG cyclodextrin phosphate, PEG sorbitan phosphate, PEG alkyl sorbitanphosphate, and PEG methyl glucoside phosphate. Suitable non-polymericphosphates include alkyl mono glyceride phosphate, alkyl sorbitanphosphate, alkyl methyl glucoside phosphate, alkyl sucrose phosphates.The unwanted tastes often associated with these surfactants are soapy,chemical, and/or artificial.

Water-soluble amphoteric surfactants useful herein further include amineoxide surfactants. Amine oxides are the result of oxidation of tertiaryamines, typically C12-C18 alkyl dimethyl, N-oxides. For example, amineoxide surfactants useful herein may include lauryl dimethyl amine oxide;lauryl dihydroxyethyl amine oxide; cocamidopropyl amine oxide;Lauramidopropylamine oxide; cetyl dimethyl amine oxide;3-Lauramidopropyl-N,N-dimethylamine oxide.

In one embodiment, the water-soluble surfactant is selected from alkylphosphate surfactants, alkyl phosphate ethoxylated surfactants, laurylsulfate surfactants, betaine surfactants, betaine ethoxylatedsurfactants, amine oxide surfactants, and mixtures thereof. In anotherembodiment, the water-soluble surfactant is selected from alkylphosphate surfactants, alkyl phosphate ethoxylated surfactants, andmixtures thereof. In one embodiment, the water-soluble surfactant is amono alkyl phosphate surfactant.

In one embodiment, the surfactant is selected from cocoamidopropylbetaines, mono alkyl phosphates, ethoxylated mono alkyl phosphates, andmixtures thereof.

Water

The compositions of the present invention contain from about 3% to about90%, by weight of the composition, of water. In one embodiment, thecomposition includes from about 30% to about 90%, by weight of thecomposition, of water. In one embodiment, the compositions of thepresent invention contain from about 3% to about 20%, alternatively fromabout 60% to about 90%, alternatively from about 70% to about 80%, byweight of the composition, of water.

Undesirable Non-Polar Material

The compositions of the present invention contain less than about 4%, byweight of the water-soluble surfactant, of undesirable non-polarmaterials. The weight of the undesirable non-polar material is measuredagainst the total weight of water-soluble surfactant present in thecomposition to clearly identify the desired ratio between undesirablenon-polar material and water-soluble surfactant and to thereby avoid thedilution effect that may be present with larger amounts of water.

In one embodiment, the composition contains less than about 3%,alternatively less than about 2.5%, alternatively less than about 2%,alternatively less than about 1%, alternatively less than about 0.5%,alternatively less than about 0.25%, alternatively less than about0.15%, of undesirable non-polar materials, all by weight of thewater-soluble surfactant.

In one embodiment, the composition comprises at least 20%, by weight ofthe composition, of water-soluble surfactant and less than 1%, by weightof the composition, alternatively less than 0.5%, by weight of thecomposition, of the undesirable non-polar materials.

As used herein “undesirable non-polar materials” refers to any non-polarmaterials that are found in the water-soluble surfactant composition inneed of treatment. In one embodiment, the undesirable non-polarmaterials are selected from residual alcohols, alcohol ethoxylates,aldehydes, ethers, ketones, alkylamines, amides, amines and esters.

In one embodiment, the undesirable non-polar materials may beoff-tasting components selected from impurities, unreacted startingmaterials, by-products and/or contaminants. Such undesirable non-polarmaterials may be described by consumers as soapy, bitter, metallic,earthy or dirty, and astringent. Soapy is typically characterized by thepresence of dodecanal or dodecanol. Bitter taste may occur in thepresence of alkyl amines or alcohols.

The composition further comprises less than about 2.5%, by weight of thewater-soluble surfactant, of alcohols having a carbon chain length ofgreater than 4. In one embodiment, the composition comprises less thanabout 2%, alternatively less than about 1.5%, alternatively less thanabout 1%, alternatively less than about 0.75%, alternatively less than0.5%, alternatively less than 0.25%, alternatively less than 0.1%,alternatively less than 0.05%, alternatively less than 0.01%, by weightof the water-soluble surfactant, of alcohols having a carbon chainlength of greater than 4.

The composition further comprises less than about 1%, by weight of thewater-soluble surfactant, of amine and amide materials. In oneembodiment, the composition comprises less than 0.75%, alternativelyless than 0.5%, alternatively less than 0.25%, alternatively less than0.1%, alternatively less than 0.05%, alternatively less than 0.01%, byweight of the water-soluble surfactant, of amine and amide materials.

The composition further comprises less than about 1%, by weight of thewater-soluble surfactant, undesirable non-polar materials selected fromaldehydes, esters, ketones, and organic acids. In one embodiment, thecomposition comprises less than 0.75%, alternatively less than 0.5%,alternatively less than 0.25%, alternatively less than 0.1%,alternatively less than 0.05%, alternatively less than 0.01%, by weightof the water-soluble surfactant, of undesirable non-polar materialsselected from aldehydes, esters, ketones, and organic acids.

In one embodiment, the water-soluble surfactant is mono alkyl phosphate.In one such embodiment, the composition comprises mono alkyl phosphateand the composition further contains less than about 2.5%, alternativelyless than about 2%, alternatively less than about 1.5%, alternativelyless than about 1%, alternatively less than about 0.5%, alternativelyless than about 0.1%, alternatively less than about 0.01%, by weight ofthe mono alkyl phosphate, of alcohols having a carbon chain lengthgreater than 4.

In one embodiment, the water-soluble surfactant is a cocoamidopropylbetaine and the composition contains less than about 1%, alternativelyless than about 0.75%, alternatively less than about 0.5%, alternativelyless than about 0.1%, alternatively less than about 0.05%, alternativelyless than about 0.01%, alternatively no measurable quantity, by weightof the cocoamidopropyl betaine surfactant, of amine and amide materials.

In one embodiment, the composition contains from about 10% to about 50%,alternatively from about 20% to about 30% of the treated water-solublesurfactant, from about 30 to about 70%, alternatively from about 3% toabout 30% water, by weight of the composition and less than about 1%total alcohols, by weight of the water-soluble surfactant.

Liquid-Liquid Extraction Process

In one embodiment, the compositions herein have been subjected to aliquid-liquid extraction process. As used herein, liquid-liquidextraction, also known as solvent extraction and partitioning, refers toa standard method to separate compounds based upon their relativesolubilities in two different immiscible liquids, here, water and asolvent. It is an extraction of a substance from one liquid phase intoanother liquid phase. The “liquid-liquid” phrase refers to the twodifferent immiscible liquids that are mixed as part of the extractionprocedure. As used herein, immiscible refers to the ability of the twoliquids to form at least two layers when mixed together. The layers maybe formed after mixing the two liquids and allowing them to sit at restfor a variable period of time, or in some instances, the mixture of thetwo liquids may be centrifuged and/or cooled below room temperature inorder to assist the separation.

Typically in liquid-liquid extraction, one of the phases will beaqueous, and the other a non-polar lipophilic organic solvent such asether, MTBE, dichloromethane, chloroform, or ethyl acetate. Most organicsolvents float on top of an aqueous phase, though important exceptionsare most halogenated solvents.

Equipment typically used in a laboratory setting for liquid-liquidextraction includes a separatory funnel. In a small scale plant or lab,batch-wise liquid-liquid extraction methods may be used, such as bymixing the two liquids and then introducing them into a large scaleseparatory funnel. In larger scale plant production, a multistagecontinuous counter current extractor may be used to quickly and easilyrun multiple extractions in sequence. In one embodiment, the processincludes the use of a machine selected from centrifugal contactors, thinlayer extractors, spray columns, pulsed columns, and mixer-settlers, andcombinations thereof, in the extraction process.

In many instances, a separatory funnel has the shape of a conesurmounted by a hemisphere. It has a stopper at the top and stopcock(tap), at the bottom. Separating funnels used in laboratories aretypically made from borosilicate glass and their stopcocks are made fromglass or PTFE. Typical sizes are between 50 mL and 3 L. In industrialchemistry they can be much bigger and for much larger volumes,centrifuges are used.

To use a separatory funnel, the extraction mixture is introduced intothe separatory funnel through the top with the stopcock at the bottomclosed. The funnel is then closed and shaken gently by inverting thefunnel multiple times. The funnel is then inverted and the tap carefullyopened to release excess vapor pressure. The separating funnel is setaside to allow for the complete separation of the phases. The top andthe bottom tap are then opened and the two phases are individuallyreleased by gravitation and separately captured.

In one embodiment, the liquid-liquid extraction process will use anextraction step in which undesirable non-polar materials are transferredfrom the aqueous phase to the solvent phase and then optionally followedby a scrubbing stage in which the undesirable non-polar materials areremoved from the solvent phase, then optionally followed by a strippingstage in which any water-soluble surfactants or other materials areremoved from the solvent phase. The solvent phase may then be treated tomake it ready for use again.

In one embodiment, the process includes a step of collecting thewater-soluble surfactant from the aqueous phase. In another embodiment,after the step of collecting the water-soluble surfactant from theaqueous phase, the water-soluble surfactant is subjected to one or moreof the following:

-   -   a) at least one repeat of the process steps, optionally        repeating the steps of the process at least 3 times, optionally        repeating the steps of the process at least 4 times, in        succession;    -   b) a further filtration step, optionally using carbon        filtration; and/or    -   c) incorporation of the water-soluble surfactant into an oral        care composition.        Oral Care Compositions

The treated water-soluble surfactant compositions herein may beincorporated into an oral care composition resulting in an oral carecomposition having improved taste versus one containing an untreatedwater-soluble surfactant.

As used herein, “oral care composition” is meant a product, which in theordinary course of usage, is not intentionally swallowed for purposes ofsystemic administration of particular therapeutic agents, but rather isretained in the oral cavity for a time sufficient to contactsubstantially all of the dental surfaces and/or oral tissues forpurposes of oral activity. The oral care composition may be in variousforms including toothpaste, dentifrice, tooth gel, subgingival gel,mouthrinse, mousse, foam, mouthspray, lozenge, chewable tablet, chewinggum or denture product. The oral care composition may also beincorporated onto strips or films for direct application or attachmentto oral surfaces.

In one embodiment, the oral care composition further comprises anabrasive. Examples of abrasives useful herein include precipitatedsilica, fused silica, and mixtures thereof.

EXAMPLES Example I Improved MAP L213/S Surfactant

Undesirable non-polar materials were extracted from MAP L213/S (a monoalkyl phosphate surfactant in aqueous solution, supplied by Rhodia),using the processes set forth herein wherein ethyl acetate (supplied byHoneywell Burdick & Jackson, Muskegon, Mich., USA) was used as theextraction solvent. The extracted materials were then analyzed and thetreated MAP L213/S was evaluated for taste and odor after the extractionand shown to be very mild, especially when compared with the startingMAP L213/S material. The undesirable materials removed from the MAPL213/S commercially supplied material are set forth in Table 3, below.The following process steps were taken:

1. 100 grams of MAP L213/S were placed into a clean 250 mL separatoryfunnel.

2. 100 mL of ethyl acetate was added to the separatory funnel, which wasstoppered, and shaken vigorously for approximately 1 minute.

3. The separatory funnel contents were then rested for a period of timeuntil they ettled into two visibly distinct layers.

4. The bottom layer (treated MAP L213/S) was drained from the separatoryfunnel into a second, clean 250 mL separatory funnel.

5. The ethyl acetate was separately collected and set aside for otherpurposes.

6. A second aliquot of 100 mL of fresh ethyl acetate was then added tothe treated MAP L213/S in the separatory funnel and the steps 2-5 wererepeated for a total of 5 times.

7. After the last extraction step, the aqueous layer was collected intoa round bottom flask, which was then placed on a rotavapor (model RE111supplied by BUCHI Labortechnik AG in Flawil, Switzerland). The waterbath of the rotavapor was set at 80° C. and allowed to run until theethyl acetate odor is no longer perceived.7. The mass of the treated MAP L213/S surfactant was then obtained andwater was added to make up for any mass loss due to water loss alongwith the EtOAc removal. “To assess extraction efficiency, samples ofboth the pre- and post-extracted oral care component are analyzed viaimmersion Solid Phase Microextraction (SPME) followed by GC-MS (using anAgilent model 6890 GC & model 5973 Mass Spectrometric Detector, AgilentTechnologies, Wilmington, Del., USA). Compare the impurity peak area inthe pre- and post-extracted samples to determine the efficiency of theirremoval.”

TABLE 3 Results of Mono alkyl phosphate LLE treatment with EtOAc AreaControl (Pre- Reduc- Undesirable Retention extract) Peak Post Extracttion Material Time (Min) Area Peak Area (%) Undecane 3.39 1216114 0100.0 Dodecene Isomer 4.35 3218343 0 100.0 Dodecene Isomer 4.42 34506180 100.0 Dodecene Isomer 4.46 2311369 0 100.0 Dodecene Isomer 4.574329376 0 100.0 Dodecene Isomer 4.66 2547216 0 100.0 Tridecene Isomer5.09 2406145 0 100.0 Tridecene Isomer 5.15 1220445 0 100.0 TrideceneIsomer 5.19 438095 0 100.0 Tridecene Isomer 5.29 1367495 0 100.0Tridecene Isomer 5.38 1114436 0 100.0 Tetradecene Isomer 5.45 674727 0100.0 Tetradecene Isomer 5.52 1030783 0 100.0 Tetradecene Isomer 5.591218184 0 100.0 Tetradecene Isomer 5.63 1589820 0 100.0 TetradeceneIsomer 5.77 573418 0 100.0 Tetradecene Isomer 5.80 220422 0 100.0Tetradecene Isomer 5.83 184627 0 100.0 Tetradecene Isomer 5.88 300141 0100.0 Tetradecene Isomer 5.97 199647 0 100.0 Tetradecene Isomer 5.99175759 0 100.0 Tetradecene Isomer 6.06 177721 0 100.0 Pentadecane 6.22669888 0 100.0 Methyl 4,6- 6.61 1023628 0 100.0 decadienyl etherHexadecane 6.83 1645290 0 100.0 Dodecanal 7.57 2654710 129439 95.1Unknown 7.60 776038 0 100.0 Unknown 7.64 1108611 0 100.0 Unknown 7.701879031 0 100.0 Methyl 6,8- 7.80 1223734 0 100.0 dodecadienyl etherUnknown 7.84 1463962 0 100.0 Unknown 7.95 3115904 0 100.0Butyl-substituted 8.04 5371992 0 100.0 tetrahydrofuran Branched alcohol8.29 1323195 0 100.0 Branched alcohols 8.38 4633193 0 100.0 Branchedalcohols 8.48 8500950 0 100.0 Dodecanol 8.88 101956289 932638 99.1Ethylene glycol 10.23 55816598 522217 99.1 mondodecyl ether Diethyleneglycol 12.00 31588284 560933 98.2 monododecyl ether Triethylene glycol14.90 8518697 264967 96.9 monododecyl ether Average % 99.7 Reduction

The resulting treated MAP L213/S having a composition according to thepresent invention was then subjected to comparative taste testing asfollows:

The following MAP L213/S compounds (all based upon the MAP L213/Ssurfactant commercially available from Rhodia) were subjected to a 6person panel for tasting. Each MAP material was diluted to a level of 1%surfactant in distilled water and neutralized to pH 7. 10 mL sampleswere provided in 15 mL cups to the panelists. Panelists were instructedto not sample materials more often than once in the morning and once inthe afternoon in order to provide enough time for the palate to clearbetween samples and were instructed to not eat or drink within 15minutes before sampling. The panelist was instructed to empty thecontents of the cup into their mouth without swallowing, swish theproduct for 10-20 seconds, expectorate, wait 10-20 seconds, and thenrate their perceptions for the following categories on a scale of 0 to60:1) soapy taste; 2) bitterness amount; 3) other off-taste amount; 4)“soapy taste” intensity; 5) “bitter taste” intensity.

176=Rhodia L213/S, lot SW10G-4636 251=Rhodia L213/S, lot 012

389=Rhodia L213/S, lot 010

462=Rhodia L213/S, lot 011

937=Rhodia L213/S, lot 001 extracted with ethyl acetate pursuant to theprocess steps set forth above in this Example I

Control=Rhodia L213/S, lot 001

As may be seen in Table 4, the control and the comparative examples 176,251, 389, and 462, all had significantly higher ratings for negativetaste elements such as the soapy taste, bitterness amount, otheroff-taste amount, soapy taste intensity, and bitter taste intensity thanthe MAP composition treated with ethyl acetate according to theprocesses set forth herein.

TABLE 4 Attribute n = 6 176 251 389 462 937 CTL (Comp) (Comp) (Comp)(Comp) (Example I) Soapy 41.25 47.50 33.75 30.42 38.75 12.50 TasteBitterness 32.50 44.08 42.08 39.58 44.58 5.83 Amount Other 32.50 34.0024.58 26.25 26.08 3.75 Off-taste Amount “Soapy 42.08 45.00 32.00 28.7539.25 7.50 Taste” Intensity “Bitter 31.25 39.17 41.25 38.75 42.92 3.17Taste” Intensity

Example II Improved Cocoamidopropyl Betaine Surfactant

Undesirable non-polar materials were extracted from cocoamidopropylbetaine surfactant, supplied by Stepan, Mexico SA DE CV (Matamoros, MX),using the process steps shown in Example I, except that 20 gramscocoamidopropyl betaine and 20 mL of solvent were used (in place of 100grams of MAP and 100 mL of solvent) and only 3 repetitions (stages) ofsteps 2 through 5—substituting the cocoamidopropyl betaine for the MAPL213/S. The extracted materials were then analyzed and the treatedcocoamidopropyl betaine surfactant was evaluated for taste and odorafter the extraction and shown to be very mild, especially when comparedwith the starting material. The undesirable materials removed from thecommercially supplied material are set forth in Table 5, below.

TABLE 5 Cocoamidopropyl Betaine - Pre and Post 3 Stages of EtOAcExtraction Area Control (Pre- Reduc- Retention extract) Peak PostExtract tion Impurity Time (Min) Area Peak Area (%) — — — — — Cyclohexylbenzene 7.43 421510 0 100.0 Dodecanal 7.57 2718310 91634 96.6 Methyldodecanoate 8.04 3597403 12025 99.7 Benzyl alcohol 8.52 11186150 37037196.7 Tetradecanal 8.70 396280 0 100.0 Dodecanol 8.87 1590140 319173 79.9Methyl 9.11 515756 0 100.0 tetradecanoate Biphenyl 9.19 2524375 0 100.0Diphenyl ether 9.28 8312954 0 100.0 Tetradecanol 9.86 264984 0 100.0Unknown 10.16 1794756 570477 68.2 N,N- 10.85 737881 0 100.0 Dimethyl-dodecanamide Benzoic Acid 11.13 627445 70858 88.7 Dodecanoic acid 11.237295585 295959 95.9 N,N- 11.83 300264 0 100.0 Dimethyl- palmitamideTetradecanoic acid 12.26 2070533 93129 95.5 Dodecanamide 12.80 378693 0100.0 Unknown 13.66 948057 515784 45.6 Tertiary alkyl 14.26 1761483495040 71.9 dimethylamine Average % 91.5 Reduction

Example III Improved Lauryl Betaine Surfactant

Undesirable non-polar materials were extracted from lauryl betainesurfactant, supplied by Mason Chemical Company (Arlington Heights, Ill.,USA), using the process steps shown in Example I, substituting thelauryl betaine for the MAP L213/S and only four repetitions of steps(stages) 2 through 5 were completed. The extracted materials were thenanalyzed and the treated lauryl betaine surfactant was evaluated fortaste and odor after the extraction and shown to be very mild,especially when compared with the starting material. The undesirablematerials removed from the commercially supplied material are set forthin Table 6, below.

TABLE 6 Lauryl Betaine - Pre and Post 4 Stages of EtOAc Extraction AreaControl (Pre- Reduc- Retention extract) Peak Post Extract tion ImpurityTime (Min) Area Peak Area (%) Dodecene Isomer 4.14 268607 0 100.0Dodecene Isomer 4.25 269099 0 100.0 Dodecene Isomer 4.36 100143 0 100.0Dodecene Isomer 4.42 249301 0 100.0 Dodecene Isomer 4.51 210691 0 100.0Dodecene Isomer 4.61 533604 0 100.0 Dodecene Isomer 4.68 77816 0 100.0Tertiary Alkyl 5.83 119401 0 100.0 Dimethyl amine Tertiary Alkyl 6.11110815 0 100.0 Dimethyl amine 2-Ethyl-1-hexanol 6.18 197861 0 100.0N,N-Dimethyl-1- 7.05 12603358 1716473 86.4 dodecanamine Average % 98.8Reduction

Example IV Dentifrice Compositions

Dentifrice compositions according to the present invention are shownbelow as Examples IVa-IVi in Table 7. These compositions containsurfactants resulting from the process set forth herein in ExamplesI-III. Such compositions have improved taste versus compositionscontaining the untreated commercially available water-solublesurfactants.

TABLE 7 Dentifrice Compositions Ingredient IVa IVb IVc IVd IVe IVf IVgIVh IVi Carbomer 956 0.2 0.3 0.2 0.2 0.2 0.2 0.2 CMC 0.75 0.2 1.0 1.01.0 1.0 Color Solution (1%) 0.05 0.05 0.50 0.75 0.18 0.02 0.25 0.05 0.05Wintergreen Spice Flavor 0.15 Fruit Mint Flavor 0.55 Mint Flavor 0.590.45 0.42 1.0 1.2 1.0 1.0 Cinnamon Flavor 0.5 WS-23 0.02 0.05 0.02 WS-30.02 0.05 0.02 MGA 0.2 Menthol 0.52 0.55 0.56 0.15 0.58 G-180 0.01 0.030.015 0.004 0.01 0.01 0.03 0.008 0.02 Potassium Sorbate 0.004 0.0080.004 0.004 Poloxamer 407 1.0 0.2 0.2 0.2 0.2 0.2 Polyethylene Glycol300 3.0 3.0 3.00 Polyethylene Glycol 600 2.3 Propylene Glycol 10.0Sweetener 0.46 0.5 0.45 0.4 0.58 0.4 0.4 0.4 0.4 Silica Abrasive 22.031.0 20.0 21.0 17.0 15.0 15.0 15.0 15.0 Sodium Benzoate 0.004 0.0040.004 0.004 Silica Thickening 2.0 7.0 7.0 7.0 7.0 Sodium Bicarbonate1.50 9.0 Sodium Carbonate 0.50 NaOH 50% Soln 1.74 2.20 2.0 2.0 2.0 2.0Na Lauryl Sulfate 4.0 5.0 3.0 4.0 4.0 3.0 2.0 according to Example IVSodium Fluoride 0.243 0.243 0.243 Sodium MFP 0.76 0.76 0.76 0.76 0.760.76 Glycerin USP 99.7% 9.0 11.9 33.0 9.0 Sorbitol Soln USP 24.3 24.54.0 44.7 56.9 43.0 43.0 40.0 38.0 Tetra Na 2.05 5.045 3.85 3.85Pyrophosphate, Anhydrous Tetra Potassium 6.38 Pyrophosphate (60% Soln)Na Acid 2.1 4.0 1.0 4.3 4.5 4.5 2.0 Pyrophosphate Mono Alkyl 3.5 6.7 3.53.5 Phosphate according to Example I Cocamidopropyl 3.5 Betaine (30%soln) according to Example II Titanium Dioxide 0.5 1.0 0.25 0.3 0.3 0.20.2 TiO₂/Carnauba Wax 0.6 0.3 Prills Xanthan Gum 0.6 0.4 0.45 0.7 0.30.3 0.3 0.3 Water QS QS QS QS QS QS QS QS QS

Example V Improved Amine Oxide Surfactant

Undesirable non-polar materials were extracted fromN,N-Dimethyldodecylamine N-oxide (amine oxide) surfactant (−30% aqueoussolution), supplied by Sigma-Aldrich Corporation (St. Louis, Mo., USA),using the process steps shown in Example I, substituting the amine oxidefor the MAP L213/S. Additionally, a different rotary evaporator (modelEL131 supplied by BUCHI Labortechnik AG in Flawil, Switzerland) was usedfor removing residual EtOAc. During rotovap, a vacuum was also appliedvia rough pump (General Electric model SKC36PN435GX, Fort Wayne, Ind.,USA), which was controlled by manual adjustment of a clamp added to ateed in segment of hose between the pump inlet and rotovap. Vacuum wasincreased to the point where surfactant began gentle bubbling. Byapplying vacuum, the rate of residual EtOAc removal was significantlyincreased. The pre- and post-extraction amine oxide materials were thenanalyzed by immersion SPME GC-MS (Agilent model 7890 GC & model 5975Mass Spectrometric Detector, Agilent Technologies, Wilmington, Del.,USA), and the treated amine oxide surfactant was evaluated for taste andodor after the extraction and shown to be very mild, especially whencompared with the starting material. GC-MS analyses for this examplewere performed at a later time with newer equipment and the resultingretention times are slightly longer than for other examples. Theundesirable materials removed from the commercially supplied materialare set forth in Table 8, below.

TABLE 8 Results for Amine Oxide LLE treatment with EtOAc RetentionControl (Pre- Area Time extract) Peak Post Extract Peak ReductionUndesirable Material (Min) Area Area (%) Decane 3.45 729450 0 100.0 N,N-4.198 5799292 0 100.0 Dimethylhydroxylamine Undecane 4.326 1.58E+08 0100.0 Undecene Isomer 4.613 2433592 0 100.0 Undecene Isomer 4.663 5149240 100.0 Undecene Isomer 4.696 4576558 0 100.0 Undecene Isomer 4.7313314628 0 100.0 Undecene Isomer 4.873 13478025 0 100.0 Undecene Isomer4.981 7185801 0 100.0 Dodecane 5.262 97542837 275259 99.7 DodeceneIsomer 5.517 1722855 0 100.0 Dodecene Isomer 5.564 256787 0 100.0Dodecene Isomer 5.594 1970807 0 100.0 Dodecene Isomer 5.637 1.34E+0820278565 84.9 Dodecene Isomer 5.686 1713571 0 100.0 Dodecene Isomer5.749 5157893 0 100.0 Dodecene Isomer 5.847 2337409 0 100.0 Tridecane6.079 60387770 0 100.0 Substituted Tetrahydrofuran 6.211 741293 0 100.0Tridecene Isomer 6.304 934388 0 100.0 Tridecene Isomer 6.373 2370074 0100.0 Tridecene Isomer 6.411 1509006 0 100.0 Tridecene Isomer 6.5145357518 0 100.0 Tridecene Isomer 6.61 2493787 0 100.0 Tetradecane 6.80888989028 0 100.0 Tetradecene Isomer 7.013 648872 0 100.0 TetradeceneIsomer 7.075 793547 0 100.0 Tetradecene Isomer 7.119 51889810 629899787.9 Methyl Tetradecane Isomer 7.184 1406294 0 100.0 Tetradecene Isomer7.209 1387502 0 100.0 Tetradecene Isomer 7.301 1082259 0 100.0Pentadecane 7.469 10662978 0 100.0 Unknown 7.683 3450057 0 100.0 Methyl4,6-decadienyl ether 7.863 19513653 0 100.0 Hexadecane 8.094 34907941 0100.0 Undecanone Isomer 8.166 258835 0 100.0 N,N-Dimethyl-1- 8.30476976187 228611 99.7 Dodecanamine Undecanol 8.381 5483997 0 100.0Dimethyl Undecanone 8.421 1533470 0 100.0 Dodecanone Isomer 8.582 3942390 100.0 Heptadecane 8.681 4445134 0 100.0 Dodecanone Isomer 8.783 5377290 100.0 Dodecanal 8.824 16858547 3586725 78.7 SubstitutedTetrahydrofuran 8.956 4420861 0 100.0 Methyl 6,8-dodecadienyl 9.05613713367 0 100.0 ether Octadecane 9.238 23859062 0 100.0 Dodecanoicacid, methyl 9.303 6560940 0 100.0 ester N,N-Dimethyl-1- 9.358 260948043499984 86.6 Tetradecanamine Tetradecanone Isomer 9.737 1458218 0 100.0Nonadecane 9.768 1489949 0 100.0 Unknown Amide 9.864 255865 0 100.0Tetradecanone Isomer 9.923 589980 0 100.0 Unknown Amide 10.048 341466 0100.0 Dodecanol 10.137 40526459 856635 97.9 Pentadecanone Isomer 10.2734602974 0 100.0 Methyl tetradecanoate 10.374 1435045 0 100.0Pentadecanone Isomer 10.451 1668318 0 100.0 Tetradecanol 11.128 98749280 100.0 N,N-Dimethyldodecanamide 12.113 44118371 65123 99.9p-Dicyclohexylbenzene 12.445 2523931 0 100.0 N,N- 13.048 14118245 67931295.2 Dimethyltetradecanamide Dodecanoic acid ester 14.154 24988729 0100.0 Dodecanoic acid ester 15.662 2168393 0 100.0 Avg % Reduction =98.9

The dimensions and values disclosed herein are not to be understood asbeing strictly limited to the exact numerical values recited. Instead,unless otherwise specified, each such dimension is intended to mean boththe recited value and a functionally equivalent range surrounding thatvalue. For example, a dimension disclosed as “20 g” is intended to mean“about 20 g.” All percentages, ratios and proportions herein are on aweight basis unless otherwise indicated. Except as otherwise noted, allamounts including quantities, percentages, portions, and proportions,are not intended to indicate significant digits.

It should be understood that every maximum numerical limitation giventhroughout this specification includes every lower numerical limitation,as if such lower numerical limitations were expressly written herein.Every minimum numerical limitation given throughout this specificationwill include every higher numerical limitation, as if such highernumerical limitations were expressly written herein. Every numericalrange given throughout this specification will include every narrowernumerical range that falls within such broader numerical range, as ifsuch narrower numerical ranges were all expressly written herein.

Except as otherwise noted, the articles “a”, “an”, and the mean “one ormore”.

As used herein, “comprising” means that other steps and otheringredients which do not affect the end result can be added. This termencompasses the terms “consisting of” and “consisting essentially of”.The compositions and methods/processes of the present invention cancomprise, consist of, and consist essentially of the essential elementsand limitations of the invention described herein, as well as any of theadditional or optional ingredients, components, steps, or limitationsdescribed herein.

Every document cited herein, including any cross-referenced or relatedpatent or application, is hereby incorporated herein by reference in itsentirety unless expressly excluded or otherwise limited. The citation ofany document is not an admission that it is prior art with respect toany invention disclosed or claimed herein or that it alone, or in anycombination with any other reference or references, teaches, suggests ordiscloses any such invention. Further, to the extent that any meaning ordefinition of a term in this document conflicts with any meaning ordefinition of the same term in a document incorporated by reference, themeaning or definition assigned to that term in this document shallgovern.

While particular embodiments of the present invention have beenillustrated and described, it would be obvious to those skilled in theart that various other changes and modifications can be made withoutdeparting from the spirit and scope of the invention. It is thereforeintended to cover in the appended claims all such changes andmodifications that are within the scope of this invention.

What is claimed is:
 1. An oral care composition comprising from about 3%to about 90%, by weight of the composition, of water and an alkylphosphate ethoxylated surfactant exhibiting improved taste wherein thealkyl phosphate ethoxylated surfactant comprises: a) less than about0.1%, by weight of the alkyl phosphate ethoxylated surfactant, alcoholshaving a carbon chain length greater than 4; b) less than about 1%, byweight of the phosphate ethoxylated surfactant, of aldehydes, esters,ketones, and organic acids; and c) less than about 1%, by weight of thephosphate ethoxylated surfactant, of amine and amide materials.
 2. Acomposition according to claim 1 wherein the composition comprises lessthan about 0.01%, by weight of the alkyl phosphate ethoxylatedsurfactant, of an alcohol having a carbon chain length greater than 4.3. A composition according to claim 1 wherein the alkyl phosphateethoxylated surfactant is substantially free of dodecene isomers.
 4. Acomposition according to claim 1 wherein the alkyl phosphate ethoxylatedsurfactant is at least about 30% soluble in water.
 5. A compositionaccording to claim 1 wherein the composition comprises from about 10% toabout 50%, by weight of the composition, of alkyl phosphate ethoxylatedsurfactant.
 6. A composition according to claim 1 wherein thecomposition comprises from about 3% to about 20%, by weight of thecomposition, of water.
 7. A composition according to claim 1 wherein thecomposition comprises less than about less than 0.05%, by weight of thewater-soluble surfactant, of alcohols having a carbon chain length ofgreater than
 4. 8. A composition according to claim 1 wherein thecomposition comprises less than about 0.5%, by weight of the phosphateethoxylated surfactant, of aldehydes, esters, ketones, and organicacids.
 9. A composition according to claim 1 wherein the compositioncomprises less than about 0.1%, by weight of the phosphate ethoxylatedsurfactant, of aldehydes, esters, ketones, and organic acids.
 10. Acomposition according to claim 1 wherein the composition comprises lessthan about 0.01%, by weight of the phosphate ethoxylated surfactant, ofaldehydes, esters, ketones, and organic acids.
 11. A compositionaccording to claim 1 wherein the composition comprises less than about0.5%, by weight of the phosphate ethoxylated surfactant, of amine andamide materials.
 12. A composition according to claim 1 wherein thecomposition comprises less than about 0.1%, by weight of the phosphateethoxylated surfactant, of amine and amide materials.
 13. A compositionaccording to claim 1 wherein the composition comprises less than about0.01%, by weight of the phosphate ethoxylated surfactant, of amine andamide materials.
 14. A composition according to claim 1 wherein the oralcare composition is a dentifrice.